An important goal of urban ecology is determining what differentiates urban-tolerant populations of birds from their non-urban ancestors and urban-intolerant species. One key to urban success may be reacting appropriately to human activity, and the degree to which birds view humans as threats can be quantified by their escape behavior. Understanding individual-level plasticity, however, requires the tracking of known individuals. We compared flight-initiation distances (FID) and distances fled (DF) from approaches by a human between an urban and a non-urban population of individually marked Dark-eyed Juncos (Junco hyemalis) in Southern California. The urban population is more tolerant to people as evidenced by attenuated FIDs and DFs relative to non-urban birds. Although individual urban birds either habituated or sensitized to repeated approaches, there was no significant pattern at the population level. Overall, the behavioral patterns exhibited by this urban population of juncos is more supportive of in situ evolution of tolerance than either being a biased sample from an ancestral non-urban population or intrinsic behavioral plasticity that produces a uniform adjustment to urban life.